Tuesday, February 22, 2011

Much to my own disgust, I am a 16-year-old virgin. I do, however, have this person of the opposite gender with whom I makeout on weekends and at parties (and tactlessly ignore out of awkwardness at school). So yesterday, we were hooking up naked in the backseat of his car and he was fingering me. And, in the midst of his heavy breathing and inept poking, I had an amazing epiphany: I had no idea if I was actually enjoying myself. I have never had an orgasm, have no idea how to masturbate (despite pathetic attempts) and have really no inkling of how my own sexuality works. I don’t consider myself repressed and I’m really planning on losing my virginity soon. But I really don’t want to buy into the ridiculous myth that a girl’s first time has to hurt; I want to have fun. And if being fingered really doesn’t do that much, how will sex be any different?

Essentially, I’m terrified of having Female Sexual Dysfunction. I’m into this guy and I know what being horny feels like, but that’s about it. Any advice?

I don't pretend to fully comprehend the hyper-sexualized culture of today's teenager, what with the cuddle puddles, rainbow parties, and jelly bracelets, but if I have to read, "Much to my own disgust, I am a 16-year-old virgin" from any young woman ever again I'm going to firebomb Viacom, Wenner Media, and any other corporation feeding off the emotional insecurities of the teenage girl.

While I'm upset and concerned about the pressure put on today's young girls I'm going to try to put aside my anger at the moment (as I try not to think about my niece and young cousins) and endeavor to address your questions as best I can.

The first time I had sex was in the backseat of a used 1990 Nissan Pathfinder I had purchased with my Bar Mitzvah money. Ten minutes into our condom-sex she asked if I could hurry up. When I asked why, she informed me that she has a "misshapen canal" and if I could finish already "that would be great." While I had no fucking idea what these words meant at the idiot-age of 17 ("canal? Like the Suez?") they did not prevent me from paging my best friend to excitedly tell him I had lost my virginity. Yes, I felt ebullient and very American, but I mention this because this ridiculous farce of my first time had absolutely zero bearing on my sexual maturation.

I wouldn't dream of passing judgement and saying when it's right or when it's wrong to lose your virginity, but I will say that fingering is absolutely nothing like sex. Not even close. You're clearly a smart girl, so you're right not to assume anything about how your sexuality works at the moment. But I'd ask if there's any way you could apply your obvious intelligence to your fears and to ask yourself whether they truly have any basis, ya know? It's just that in my experience it's easy to be fearful of things we haven't realized yet. I was scared my entire adolescence I would never grow beyond my then small stature and that for the rest of my life I would always lose out to everyone taller in everything. I wouldn't want to diminish your fears — they shape who we are, one way or another — but it's very, very important to at least recognize that at this point they remain only that, fears and not reality.

Alas, as mostly everyone in the room will agree, sex probably won't feel good for quite some time. You simply don't know your body fully and truly yet and MORETHANANYTHING no guy your age will be the least bit competent for the next five to six years, IF EVER. The vast majority of guys who are good in bed each had a girl to teach them how with the ever-present assistance of Professors Trial and Error. Ideally this takes the form of a long term (1-2 year) relationship in college wherein after a lot of fumbling a guy learns how to please a woman and also learns that none of this entails the porn-based assumptions he entered into the sexual relationship with. It's almost comedic. They learn how to use their hands, their fingers, where the clitoris is, how to go down on their girlfriends, the power of slow-teasing and to remember to actually kiss their girlfriend during sex. Any single person you go to school with who says they are having great sex isn't lying necessarily — they simply don't know any better.

And I want to briefly touch upon "planning to lose my virginity soon." No bullshit (and this is anonymous, so I have no reason to say any kind of bullshit), but some of the fucking coolest girls I know to this very day didn't lose their virginity when they were in high school. Many were in college, some even after, and you wouldn't know it from meeting them. (Or, umm, from having sex with them.)

I'm a single, 24-year-old woman with limited dating experience. I'm attractive enough, intelligent, and generally an interesting and nice enough person, and usually have high standards for the guys that I date. Up until now, I haven't wanted to have sex outside of a committed relationship; it wasn't a moral issue, it was more of a I'm-not-comfortable-being-that-intimate-with-someone-whose-last-name-I-don't-know issue. Given that I broke up with my last boyfriend in August, I started thinking about loosening my self-imposed restrictions on physical intimacy.

Last week, I went out on a first date with a seemingly nice guy and proceeded to take him home with me. Before getting too deep (ahem) into things, I asked him when the last time he got checked for STDs was; he said it was two partners ago. I told him that in that case, though I would like to have sex with him, I just wasn't comfortable until he got tested; he said he had been thinking about doing that on his own lately, and would probably do it soon. Flash forward to date number three, a mere week and change later. After starting to get hot and heavy, the guy said that my comments about getting tested for STDs made him uncomfortable; he felt that if he acquiesced, he would be giving me the idea that we were further along in a relationship than he was comfortable being. This is after I made it clear that I was looking for a fun, casual dating situation, no real relationship required. Apparently having sex on the first date would have been no big deal, but having safe sex on the third date would be akin to an engagement ring?

Am I wrong in wanting sex but also wanting to make sure I'm not going to contract any life- or fertility-threatening infections along the way? Or can a girl only get safe sex in a relationship these days? I was proud of myself for being both honest about what I wanted (sex) while also being empowered enough to protect myself, but now I'm not so sure. I understand that condoms can go a long way towards preventing the transmission of many diseases, but I'm not comfortable with the risks that come along with condoms breaking, infections that can be transmitted in ways other than through sexual fluids, and other non-zero-risk situations.

Real easy — don’t do anything you don’t want to do! If you don’t feel comfortable having sex until someone has been tested at the start of your relationship, so be it. Some guys will be cool, some won’t! But that’s with everything!

I’m a little unclear about the “a fun, casual dating situation” you seek, but I still stick with the above. About this particular guy, however? WOW what he said was super, super lame. What bad Chuck Palahniuk book are these guys stealing their lines from? My advice would be to stop seeing him and find someone who's respectful of your concerns regardless of what date number it may be.

However I’d be remiss not to mention that using newly purchased condoms (ideally that are away from direct sunlight in the store they are purchased in) that contain spermicidal lubricant in conjunction with a water-based lubricant is a highly, highly effective way to prevent pregnancies and STDs and is unlikely to break. If he uses two condoms (the friction will cause breaking) or there is not proper lubrication then you run this risk of them breaking, but should you want to have casual sex I would recommend this regimen here.

In all of my years of having sex with ex-boyfriends and guys I dated, I have never been able to orgasm without a toy. In fact, I bought a Bullet for the first time 4 years ago just so that I could orgasm while having sex. Actually, I take that back — there was one time that I almost came without the use of a toy, but it was a hot and steamy nearly-two-hours of raw and mindless fucking with my ex, but his housemate came home and the feeling just died. So no, I've never orgasmed without one, and I don't mind not orgasming, but the guy I'm dating right now wants so much for me to be able to orgasm, preferably with him inside me; but if not, that's OK as long as he can shove it in there while I orgasm from my Bullet.

So here's the problem: it takes forever for me to be able to orgasm with another person next to me, because I do get self-conscious and I have to position myself certain ways to get that feeling. But he insists on me getting there anyway because it turns him on a lot to hear my O, and something about if I don't orgasm, it makes him feel like he's not satisfying me enough so he's unable to finish himself in the end. The few times that I agreed to use the Bullet took a long time for me to orgasm, and I feel like this might become a problem as I feel like he is going to get tired eventually of waiting around for my O. But anyway, I don't know what to do. I like the guy a lot, he is wonderful and caring, and the sex and fucking is great when I don't have to orgasm. Could it be because of our age difference — he's in his mid-30s so maybe his take/goal in sex is a bit different than mine? Is there any other way to tell the guy "Please, just pretend I'm a rag doll and fuck the shit out of me without caring about my orgasm"? Because everything I've said hasn't worked!

Every vagina was not made equal. (Here is a handy and NSFW chart.) I have dated the girl (uncannily exactly like you) who needs to use a toy (uncannily exactly a bullet) during sex to get off, and the girl who only gets off when I use my fingers, and the girl who has to hold back on all three of her orgasms because they happen too quickly. Alex Baldwin’s paterfamilias in Outside Providence was plain wrong when he said, “Sex is like Chinese food, it ain’t over to both of you get your cookies.”

So my initial reaction to you (my possible ex-girlfriend you) was to simply respond with, “What do you want me to say? As even you explicitly say yourself above — there are some of us guys who have realized that sex for women can feel incredible regardless of whether it culminates in an orgasm for them or not, and there are some guys who haven’t realized this and take it personally when the girl can’t because they're insecure. Just be open and tell him how you feel. Sure. Say the above. Done n’ done.” And while this still remains my reaction I’m gonna take a step back and do a little deeper dive into the issue at large.

I hope you have all had the opportunity to read some of the women's questions over the past few months that myself and the other intelligent handsomes that comprise this A Dude Squad receive and answer. I’ve read a lot of them. So much so that I fear even I’ve never had an orgasm and that my vagina tastes like pennies. And as you read them more and more you see some consistencies emerge. While not all women have had EXACTLY the same experience, the majority of the questions seek simple elucidation on the typically selfish, put-upon expectations/assumptions from the men in their lives. This is very upsetting to me. Selfishly, because a lot of these guys are boat-shoe-shuffling detriments to my gender who still get to have sex with awesome girls, thus perpetuating and reinforcing their behaviors. Less selfishly, because everyone deserves true and unfettered happiness. And there is never any reason why someone’s expectations (and not the realities) should encumber this. He expects you to have an orgasm? He expects you to have a threesome? He expects that you should just simply buy his bullshit logic on concerns of yours? Sorry, all that’s on HIM. It’s not on you. It’s NOT on you to have to SAY SOMETHING. It’s NOT on you to have to DO SOMETHING. It’s on THEM to realize that it’s not about THEM.

Sometimes I wish you guys could put you and your boyfriends on the phone with me. I can also invite my cool-as-hell girlfriend and my probably-once-cool mom (who both read this!) if you would like. But someone’s gonna have to walk moms through how to use conference call and I can tell you right now it ain’t gonna be me.

Is stress a viable excuse for no sex? I've been with my boyfriend for three years and at the beginning whenever we were alone, we were very sexual. Now that I've moved in, he says stress or being tired just isn't letting him in the mood. I've dressed up, I've talked dirty, but he chuckles and kisses my forehead. Ill say I get laid maybe once a month. That just into enough for me. Thoughts? He is 24, I'm 25 so age can't possibly be it! I've told him I want more sex, I've told him I'm open to anything he wants. Communication isn't it either. Other than sex we have an all right relationship. Should it matter so much to me? He says he is trying. Shouldnt it come naturally? Literally.

Crap. So, normally my answers are couched in a certain positivity and hopefulness ('cause I like to think good things happen to good folks), but, yeah, this sounds like you’re nearing the end of the relationship. I could be wrong! A Dude isn't infallible! BUT I’m a super, super sexual guy, and even I did this kind of thing to a girlfriend once (interestingly enough, at the age of 24 also). Alas, the sad, sad reason was that I fell out of Like with her. And clearly my immature self was playing architect to somewhat gird us for our inevitable demise. Also, the misguided and immature mind of a 24-year-old (I don’t care how seemingly mature they think they are at that age, they're not!) thinks that planting the seeds of concern will grow into sprigs of resentment and that this will somehow make it easier for you when the relationship sours past the point of reconciliation. It’s the fucking dumbest, most self-concerned delusion of "being a good guy" EVER. And I’m incredibly embarrassed to admit it’s something I’ve done.

AND! I’ve also been on the other side. Long term relationship. Hung out seven days a week. But regardless of our proximity she just stopped having sex with me. I would masturbate in the shower every morning. (And I hate doing that standing up.) I said the exact same thing you did, “Should it matter so much?” I told myself that she’s not really an affectionate person in the first place and I’ve had enough sexual experiences to last me a lifetime and so what if that’s my only complaint. Then she broke up with me, crushed me, within a few weeks time. As I expected in the back of my mind she would.

Don’t get it twisted. Sex is very important to a relationship. Physicality, closeness, affection, all that.

I hope that I’m wrong about where your relationship is heading, but I fear that I’m not.

OK. Let me preface this by saying that I know it is wrong to snoop — WRONG!

Now: a couple months ago, I received an anonymous email from someone saying that my boyfriend had replied to her personal ad on craigslist. This person didn't specify the type of relationship that she was seeking, but she did include the text of my boyfriend's response to her ad. His response consisted exclusively of his "stats" and the typical "are you for real?" inquiry ... it makes me think it was about sex. Anyway, he denied doing it but he seemed twitchy, and he did admit that sometimes he longs for the single life (we've been together for about a year and a half). So already I'm ... somewhat distrustful.

(Side note: I don't know how this person even figured out that I was the one to email about this: the boyfriend and I aren't even "Facebook official.")

Then I went to check my email on his computer a while ago and it automatically logged me into his account. I don't even know the password. I was moving the mouse to click "sign out" and my eyes fell on a chat he'd had with his ex. I opened it (I KNOW!). He instigated the chat by saying "get out of my dreams!" she said something like "what did i do now?" (it was obvious to me that she wasn't flirting back), and he said "i had a dream about you, and you were so hot and being mean to me." Which in his language means she was dominating him. In bed. Then I flipped through his chats looking for other stuff he said to her (I KNOW!!) and his outbox is basically full of him trying to get in touch with her and her ignoring him or blowing him off. This makes me feel somewhat OK since he's getting nowhere with her, but clearly ... he's TRYING to get somewhere with her, right? UGH! So now I REALLY want to ask him WTF and flip out, but I came by this information completely "illegally" and so have no right to use it. Right? My question is: do I just have to sit on this until he slips up for real? Or can I bring it up (in a direct way, since I've already tried the "do you think guys can get over their exes?!?" line of questioning and he's having none of it)?

Sorry for going on and on but ... I guess I didn't know how to boil it down. This episode happened a while ago and I've been mulling in silence since then — I just don't even know where to begin and I'd rather have a good, well-thought-out argument for my feelings than blow up right away and look stupid in the end.

After reading the above account there’s little regard I’m going to give to your boyfriend. SORRY! FUCK THAT JERKFACE! While I’ll refrain from making too much fun of his dated online proclivities (60 Minutes II called, they want him to come in to re-tape a lost interview from 2002 for their archives), the dude cheated on you. Who gives a shit about what cheating actually means? “Welllllllllll, I mean they did only kiss.” “Welllllllllll she’s an ex-girlfriend and she’s still in love with him so I understand if…” If anyone in a committed relationship attempts to fuck or kiss someone else, then what’s the difference? Let’s even forego de facto and go straight to de jure — according to the law, “ATTEMPTED” is still lawful grounds for wrongdoing.

Why must so many people sully the good names of awesome relationships!? It’s simple, man. Be honest and kind, make her come and make her laugh. Everything is easier when you’re honest! When I once asked this guy I knew why he locked his phone he responded with, “'Cause I have a girlfriend.” COOL ANSWER YOU RIDICULOUS IDIOT. It would appear that you’re dating this kind of person. He always takes his phone with him to the bathroom and sometimes checks his texts in the middle of a mealtime conversation with this weird half-in-pocket-half-out move as he phumphers, “yeah, uh, huh.” It’s not cool to tell an ex “you were so hot and being mean to me.” Running into an ex and saying, “hey! you look great! How are you?” is one thing, “you were so hot in my dream” quite another.

Yeah, sure, you shouldn’t snoop. A girl once went through some old writings while I was out buying us dinner. She read a bad short story I wrote a full two tears prior (fictional, mind you) where I describe a makeout scene and for the girl I used an actual girl friend of mine’s name (Aleema. Cool fucking name, right??). She thought it was non-fiction, that I had just written it, and she interpreted it as depicting me cheating on her with Aleema and proceeded to smack the pizza out of my arms (pepper flakes everywhere!) as I entered the door. I broke up with her right there.

But you did find something, so let’s move past the whole “but I found out through ill-gotten means” part. He’s actively trying to cheat on you and you will need to have the conversation. I’m sorry, but I can’t NOT recommend breaking up with him. Every time that I write these columns I answer your questions as if you guys are one of my closest girl friends (who also ask me these kind of questions too! IRL!) and I will only give you the same advice I’d give them. And right now I’d tell them to break up with this wondrously gaping asshole of a boyfriend immediately and then to keep him the fuck away from me. 'Cause my friend is bartending, and getting into fights is sooo 2010.

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To the 16 year old who is wisely addressing sexual concerns: this dude is so so so right. As a super cool, if I don't say so myself, 29 year old woman who enjoys sex immensely, I say wait. I loved making out with my boyfriends in high school but they were, as the dude says, inept, although eager to learn. It was my college boyfriend, who already had experience, not that it matters, who very sweetly agreed to wait and do everything else with me until I was ready, and at 19, I had the best first time I think anyone could have. We continued for a year of fabulous sex, of which I'm so grateful for. Trust me, if you wait until you really really want to, and you will, you are not missing anything.
If you're going to fear anything, fear having a bad first time, that just seems like a downer.

Uh, Dude. Good advice and all, but I'd just like to point out that herpes and HPV can both be spread even with condom use. The bullshit of both viruses, though, is that testing doesn't always detect them, especially in men. So, basically, while it's not true that condoms will 100% protect you from 100% of sexually transmitted diseases, infections and viruses, it's better than nothing. And testing won't 100% protect you from 100% of sexually transmitted diseases, infections and viruses either. So to me, the moral of the story is that there's an implied risk with sex. Kind of like how there's an implied risk with leaving the house. You might get a cold or the flu if you interact with another human being in a non-sexual context. STDs are no different than any other human illness, but they have the moral stigma of sexual enjoyment attached to them.
Trying to be healthy by trying to avoid STD is completely reasonable. But it's not entirely reasonable to think that there's a way to have sex while guaranteeing that you will not get a virus, infection or disease from your partner. Using condoms will protect from the most dangerous sexually transmitted diseases, like HIV. But even being in a committed relationship is no guarantee of avoidance of STDs. Viruses can lay dormant for years, and even if your partner is faithful and has been recently tested, you can still end up with herpes or HPV in the middle of a multi-year exclusive relationship.

The bottom line is, if you end up with an STD, there's no reason it should be more upsetting than, say, getting a nasty flu that makes you puke and poop at the same time. Yeah, STDs are pretty gross, and they can be painful, but that also applies to puking and pooping at the same time. And no one feels ashamed of getting the flu. In fact, they'll probably tell their simultaneous puke/poop stories for laffs!

This is the rundown I got from the sweetest (and hottest) dude gynecologist EVER after I avoided the gyno for 3 years because of a horrid experience. That horrid experience was that I had a painful sore on my ladyparts my sophomore year of college. I went to an old lady gynecologist and explained my symptoms. She didn't even examine me - she asked how many sexual partners I'd had (4, at that point), concluded that I had herpes, and that I was a whore. She proceeded to slut-shame me, throw some "use condoms" pamphlets at me, and ordered me to leave her office. A GYNECOLOGIST DID THIS. Turns out, it probably wasn't even herpes - I've never had the same symptoms, or any symptoms similar to herpes, and the sore didn't act like a typical herpes sore. The symptoms occurred during summer in which I was riding my bike around in a skirt a lot, so it was probably just chafing and I was freaking out. Or maybe it wasn't! I've told every sexual partner since that it's possible that I have herpes, and no one has opted out. But the point is, yeah. This kind of honest, straightforward, non-shaming information is hard to come by. And that is a huge problem.

@manshan- GIIIIIRRRRLLLLLLLL. I had an ingrown hair a few years ago, and the gyno automatically went YUP PROBABLY HERPES, CLOSE YOUR LEGS, HARLOT, like yours did. I stressed myself out so much that I gave myself a UTI, which just furthered my belief in the idea that I had vagina leprosy. I probably cried for a week, until I went back to see another doctor in the office for my 6 month boob check up thing, and I asked her about the lesion in question. She was really nice about it, and said something along the lines of "man, if I could write prescriptions for bikini waxes, I probably wouldn't have this problem so much."

To add something else to this, the recommendation to use spermicidal lubricant to prevent STDs is not a good one. The use of spermicide can actually *increases* the chance of contracting an STD if you have an infected partner, because it can cause irritation that can facilitate transmission of the infectious agent.

I am sorry about your gyno experience, but I am not at all surprised because I have heard so many similar stories. While I have never personally had a herpes scare, I have been on the ledge with several people, and I definitely recommend the Savage Love podcast 195 to everyone.

@manshan, I wanted to chime in on how intelligent and reasonable your comment is. Also, I wanted to give a little more support for the guy in that question-- while it's smart to ask a casual partner when the last time s/he's been tested is, if you're asking someone to get tested, you're implying some kind of exclusivity, because if you're just "fun and casual" the test would be worthless as soon as one of you introduces a new partner into the mix, which could be really soon if he's going on other first dates with lots of other girls (not to mention that virus antibody can take up to six months to show up in blood, so new infections can go undetected). Anyway, I'm pro-STD testing and have it done regularly myself, and I think it's fine to ask, but I don't think that it's completely reasonable to *expect* a casual sex partner to get tested for you.

Trying to understand what the guy was saying about getting tested I think he meant that getting tested specifically for her would imply that the writer was the only woman he was going to be sleeping with.

First of all, AAAHHHHH, better sexual health advice in the comments than in the column! A Dude, you should be careful when the advice starts veering away from feelings and into medical stuff - fact-checking FTW!

@mysterygirl, while I think you make a good point, I'd argue that it's completely reasonable to *expect* that a casual partner refuse to put out unless you get tested.

Perfect advice. The alternative is to confront him, have him throw it back at you, and get caught in a vicious cycle of lying and spying that will continue for months or years and slowly eat away at both of you until you are both the ugliest version of yourself you can imagine, then you break up.

-as Dude correctly states, high school boys suck at it. college boys do, too, but less so.
-sex is fun and all, but you WILL invariably spend hours – nay, weeks – obsessing about pregnancy and STDs once you start having it. put that stress off for a while.
-again, sex is fun and all, but as an adult it gets a little old that most romantic/sexual situations are essentially a countdown to It. most adults, I'd say, miss the days when making out and fooling around was still fun and an end in and of itself.

I guess there's no reversing the whole "youth is wasted on the young" thing, but I pretty much guarantee that in not too many years (like, 5? 6?) you'll miss the days when jobs and sex other adult bullshit wasn't on your plate.

Addendum: if you fool around and wanna get fuckin' but aren't doing it to yourself yet, I think you may be in this for the wrong reasons? Think like A Dude: dudes touch themselves from an early age because it feels awesome, and sex feels even better. Your own quest for pleasure should be the driving force here.

wait, that Craigslist thing is so crazy. I'm just curious to know what other people think is the explanation for that, and I am sad that this very wise Dude did not have one (but I understand, no one's perfect).

Also, I would add to the 16 year old to wait until you fall in love with/greatly trust someone, not just "college" as everyone else is saying. What is it about college that is some great threshold? I'm just saying, get to know someone sexually, it doesn't matter if you're 16, 18 or 25 when that happens. Also, ditto the person who says learn to have an orgasm. Try a removable shower head if those things even exist anymore. Otherwise a vibrator.

lol! scary! i also did the bathtub tap when i was young! LMAO...never told anyone that...also i used to hump my trampoline. it had one of those inner tubes around it with the tire stem for filling it with air. totes got off on that thing a few times as a kid.

i kinda love this Dude...spot on advice.

also...16 year old girl PLEASE. DO.NOT. HAVE. SEX!! it will totally suck and then when you meet a really cool guy, and fall in love, you will *HATE* that you gave it up to some random dude you make out with on weekends...SERIOUSLY!! take all of our advice. when you are an adult, men will take you much more seriously and respectfully if you werent a total whore as a teenager! j/k on that last part, but only kinda.

WHERE WAS THIS A DUDE WHEN I WAS THROWING MY VIRGINITY OUT WITH THE TRASH AT AGE 17???? That first answer is so great! Young lass, heed his advice! You are so awesome the way you are, please don't feel disgusted by the fact that you're a virgin!!

To the lady who only gets off with a vibrator, can you maybe fake it a little? I guess that's being dishonest, but personally I think of it as showing my appreciation for what's currently happening, even if it is not getting me off. Um.

I actually only realized after the fact that the dudes probably think it is Happening For Me, but whatever. Luckily, I have mostly had sex with dudes who get me off first, so it's not like I'm going without.

Oh honey bunnies, I just want to hug you all (and you too, Dude). When I remember being 16, there was no way I was ready to have sex, and when I look at 16 year olds today they look like little kids to me! I know teens these days have too much information inundating you, but not enjoying fingering in the backseat of a car with some teenage boy does not mean you have FSD! Go home and touch yourself! Don't watch porn either !

YES to all of this. Reading that she's "disgust[ed]" with herself for still being a virgin at 16 hurts my soul. There is nothing wrong with you! I strongly suggest waiting and working on yourself in the meantime. I was just out of high school when I finally did it and there are times when I almost wish I would have waited an additional few years, if only to become more familiar with my own body.

Don't worry about whether or not you're "repressed," honey. You're a 16-year-old-virgin, it simply isn't possible.

You're 16! Nothing's wrong with you! Do whatever the hell you, want be selfish, and don't let anyone make you feel bad or ugly in anyway for it.

In the event that you're not zOMG-exaggerating! ... please please please please please stop thinking of yourself as disgusting. Real talk: After you're through with reading the hairpin's sage advice go look in the mirror. You're 100% wrong if you think you're disgusting. If there's a voice in your head telling you otherwise, try to remember that, as A Dude said, that's not you it's Viacom, Wenner Media, et al talking; hell it's not even anyone you know. Well maybe that one bitch, but fuck her anyway, amirite? Who CARES what she thinks?? I know all that's easy for me to say on the interwebs, I know that, but if nothing else convinces you, then I think everyone here would agree that the honesty, maturity, articulation, and self-awareness that comes through in your letter is enough to prove that you most assuredly are not a disgusting person. Now cut it out with that mess already, wouldja? Jesus christ....

Oh, and also you're biggest fear is complete 100% USDA Grade AA bullhockey. FSD is make-believe. There are so many ways for a woman to have an orgasm. I think like, to Dudesplain for a moment, it's been proven that there's like, I don't know, 4 different ways for each freckle you get in summer. Pretty sure my older brother taught me that one now that I think about it, and eventually he became a doctor. All jokes aside FSD is fake. Seriously. It's fake.

If you "have felt anxious before sex in the last month" then you probably have FSD (quote from the questionnaire used to gauge FSD). Hi, I'm a very healthy 25 year old dude with what I thought was a very healthy sex-life (which -ahem- I sure as shit didn't have in HS), but, devastingly, I have FSD. Like, all the time. :(

I'm a little surprised (bummed?) that no one has said this yet. Maybe the movie Orgasm Inc. is a good place for you to start, healthy 16 year old future rad lady.

16 year old: ok, this is my THIRD time writing this out (on my phone, no less); I think it's important and hopefully I won't delete my comment again! Anyway, I didn't have sex til I was 22. I didn't plan that, it just happened. And I'm sooooo glad it did happen that way! A number of my friends who had sex at the "normal" age (is that even normal????) were not psychologically ready/mature enough to deal with any fallout (teenage boys don't really know what they're doing either, sexually or emotionally). For me, the positives (no sex hang-ups, lots of confidence in bed)of waiting FAR exceeded the negatives (occasional teasing from girlfriends, worrying about if I should tell a guy that I was a V). You are clearly smart, and therefore cool, so I would advise you to ride it out for a minute and go with your gut, which seems to be telling you to hold off. Ignore the pressures of high school. You will, in a few years, realize that high school totally doesn't matter, even though it seems really important now. Watch some porn (WITHOUT men in it) to learn how to masturbate/potential sweet spots. Figure yourself out first and you'll be a lot more confident when the time comes!
p.s. Most people I've told that I waited til I was 22 think that's awesome. Girls say they wish they waited and guys think it's hot for some reason. Good luck and just think things through, whatever you do. Just know that there's no REAL (ie important, life altering) stigma attached to waiting.

Agreed! I didn't have sex until my teens were over, and I'm so glad. (I'm not usually a sharer of this information, but in case anyone here is a teenager on the fence -- waaaaaait. You're missing nothing!)

I lost my v when I was 18. It was weird and awkward and kind of sucked and I didn't do it again until I was 21. I say wait until you can't wait anymore. I had friends who just couldn't hold on to it and it seems like they enjoyed themselves a lot more than I did just trying to get rid of it. I don't think it's so much of an age thing as it is a comfort thing.

16 year old, you never mentioned why you're so disgusted by your own virginity - but since you mentioned you don't know anything about your own sexuality yet, I'm assuming it's because you have shitty friends who make you feel shitty about your virginity. Get better friends. Yours are shit. Nobody should give a shit about your virginity, much less the people you rely on for support and companionship.

I was 25 when I had sex for the first time (hate the phrase "loss of virginity," what is this, the Middle Ages?) and it was a great decision to wait that long. Basically the upshot is that I've never had bad sex in my life. Every time I've had sex I've known what I like, felt confident enough to ask for what feels good, and felt confident enough to define the terms with my partner, whether it was casual or a relationship. And of course, to make sure we had birth control and protection. (Not that this is a requirement of age, but having a job and insurance helps . . . ) I highly recommend that your first time be within a relationship with someone you trust. They can demonstrate their worthiness by dating you for a few months while you just fool around and figure out what feels good, by being mature about birth control and bodily weirdness like periods, and of course, in all the normal ways that people earn trust by like, doing what they say they will and never lying.

16 year old, you obviously wrote to the Hairpin for a reason--because you like the type of people who hang out here and can see yourself being like us when you're our age (I'm 27 for what it's worth. And female.) I think the unanimity of these responses could tell you something . . .

i had a very similar craigslist situation happen to me with my ex-boyfriend. someone emailed me to say he had been sending pictures of himself (ew) out as replies to ads posted in the casual encounters section. i confronted him and he denied it, telling me that yes, he had done it before, but not while we had been together.

however, i can get incredibly jealous and, as any 19 year old in her first long-term relationship would do, began hacking into his email. i saw him sending out email again a few months later and i couldn't do anything about it! i couldn't ADMIT i was snooping! so i let it eat away at me and would completely blow up at irrational times (while shaving my legs ["YOU DON'T DESERVE SMOOTH SKIN!", whiile ordering take-out ["WHY DO I HAVE TO MAKE THE PHONE CALL!"], etc.) instead.

in conclusion: snooping is bad, don't believe boys who say they've "stopped" sending out pictures of their dick in hopes of a threesome, and only shave your legs for those you can trust.

Yuuuuup yup yup to all these answers. I was suspicious of my ex, logged on to his e-mail (which he always ALWAYS kept suspiciously away from my eyes) and found him flirting with and planning to meet up with other girls. I kept it to myself for a month before I couldn't take it anymore, and was miserably on and off with him for months to come.

Lesson learned: I didn't trust him because he wasn't trustworthy. Break up and move on. Listen to those instincts and find someone who is open and honest and makes you come and makes you laugh. Thanks a Dude!

So, wait, am I really the only person reading this who had awesome, orgasm-inducing sex as a teenager going at it with a teenager? My first time happened when I was 17, with my boyfriend who was also 17, and it was like, whoa.

I say, if you wanna do it, go for it, and not necessarily with someone older and more experienced. Your dude's fumbly fingering isn't necessarily indicative of his potential p-in-v skillz (fingers crossed!), so as long as you feel ready and practice safe sex, have fun!

I had fun and satisfying sex at 17, with my 17-year-old boyfriend. So it is possible. But he was unusually sweet and gentle and nice, I think, so I wouldn't want to give now-17-year-olds the impression that that's typical.

I am also a member of the 17 club, though my boyfriend was 21. The first time (a Friday) I did not feel anything but the 2nd time (a Saturday) and all the times thereafter were great. As a matter of fact I enjoyed it so much that the first thing the following Monday I scheduled an appointment at Planned Parenthood for birth control.

I really don't get all the "virginity is a magikal thing" posts here. It's like getting a drivers license. It's an added responsibility but you can't beat the benefits.

Yeah, but you guys all had boyfriends, and this 16 year old makes out with a boy she ignores at school= BIG difference. I definitely had friends who lost their ladyflowers as teens while in long term relationships and are all the better for it, but I just think this gal sounds not ready, and I sure has hell wasn't at 16 (and didn't until a few years later). I think the virginity thing has more to do with being comfortable with yourself and having sex with someone you trust and communicate with more than the age thing, and, not everyone gets to have that at whatever the age.

that makes me sad. i dont think waiting will assure you that it will be awesome, but it will definetly make it a little better. and you have to understand that probably the main reason your first was "good" was because of the relationship aspect of it. i highly doubt that had you had the EXACT same sex without the emotional attachment you would classify it as "good". like HIGHLY doubt. women are emotional beings. we can rarely be turned on and fucked properly without some sort of mental and/or emotional attachment. she ignores dude at school. no way would the sex be decent.

Virgin Chick...WAIT!!! atleast until you have a semi serious relationship! emotions will make the fucking AMAZING!!

thunda look at it this way. You have added responsibility for the lives of others both behind the wheel of a car or with the capacity to give birth. And I am not one for endowing either with the sanctity of any fabricated emotions. What made my first, well make that my second, sexual experience wonderful was my boyfriend's very thick fat cock, not any emotional connection.

word. I dated an older lady (ok, she was in the next grade up, but it seemed like a lot at the time) in high school who knew what she was doing, and made sure that I did too before too long. Definitely the best educational experience of high school. All my future girlfriends should thank her for anything I may do that isn't totally awkward or mangasm-centric.

After writing that last sentence I thought about the faces of any of my girlfriends since high school, and especially the later high school girlfriend who feuded extensively with my older lady, reading that sentence. Ha! it's still true Erin. Thanks are in order.

Flipside: I started at 16 and explored the learning curve with an equally inexperienced girlfriend for the next 2 years. It was pretty cool... but I think I really got to enjoy the whole deal more much later, at 21, when I was dating an older girl who taught me I shouldn't be afraid to ask (and do) what I wanted instead of caring only about the girl's needs and second-guessing her at every turn. Then she dumped me via IM and hooked up with her ex's best friend, the end.

It's funny, this is the second time Ask a Dude has directly responded to something I've been thinking about at time of publication. In this case, it's STD testing, except I already had sex with him once? A little drunk? And now that I think about it, I'm maturing and owning my own sexuality and everything, and I've been super-lucky not to have gotten an STD so far, given my number of partners. And who knows! Maybe I have a dormant one! Anyway, I want to have both of us get an STD test. Just in case.

So, I was just walking to the train this morning thinking, "How do I bring it up?" And thanks to A Dude, I now have decided to just bring it up. And if he's an asshole about it, I don't want him putting his dick in me anyway.

Love this Dude, as all the Hairpin Dudes. Just want to toss in my two cents for sexually neglected #4. I too was once in a relationship just like this, where my boyfriend was all about boning at first, but once we got serious and started hanging out allll the time, his interest in sexytime declined rapidly until we were living together and only doing It once a month, if that. It was not because he wasn't into me or was falling out of love with me-- for one thing, he was very expressive of his love in other ways, and for another, when I finally broke up with him after a year and a half of dating, he was completely crushed and occasionally STILL tries to get me back. So while it is entirely possible that A Dude is right here, that is not necessarily the case. Unfortunately, I can't really speak to what the case may be, because I never figured out what my ex's deal was. I thought for a while he might be gay, but I've since ruled that out. All he would say when we discussed it was that he just didn't really like sex that much and the only reason he'd done it so often when we started out was to make me like him.

But since your description of your "all right" relationship sounds pretty tepid anyway, I would just dump him and go find someone to bang you as well and as often as you deserve! I too struggled the whole time during our relationship with how big of a deal the lack of sex should be, and now that the experience is several years in my past I am confident with saying that yeah, it is kind of a big deal.

Oh for Chrissakes. I'm all the way down at the bottom of this thread now, but 16 year old, if you're still reading--the ONLY thing you should take from each and every one of these individual stories is that losing your viriginity is just that: an individual choice. I was DYING to lose my virginity at 15 (so so so curious OMG) so I did. I chose a guy I liked, who I trusted, who wasn't a virgin, and who I knew I would never have to see again if it was awkward. I have never ONCE in the past decade of being a sexually active adult, regretted that decision. Only you can tell whether or not you're ready, and some hairy 20-something dude and a bunch of internet commenters are DEFINITELY not going to be able to tell you that.

So, to answer the question you actually asked: masturbate. They sell tiny vibrators in boxes of condoms now, or there's always the Sharper Image back massager, if you don't have access to a sex shop. It took me years to have an orgasm manually, but with a vibrator, I got it right away--at like, age 12. You need to learn all about your clitoris and what it likes, because you're going to need to teach a boy about it, either this boy or the next boy. Beyond that, try new things, and try everything--have him bite you, try taking control, let him take control, etc. Don't do anything you're not comfortable with, and go slow, but remember that all this stuff is normal and fun and definitely has been done by plenty of other people on the planet before, so you're not a freak for wanting to try it. You can do all these things before, during, and after you have sex for the first time, whenever that may be--sexuality is not just about p-in-v intercourse. My only unconditional, one size fits all advice is TAKE YOUR TIME--make out with him until you're really horny, and then do it some more just in case, and do the same with every step along the way. The journey is just as much fun as the destination.

Oh, and for the record--fingering never did anything for me either, until I lost my virginity. Same with most of my friends. Afterwards it got a lot more fun.

Hallmark should start a line of "thank you for teaching how to not be shit in bed" cards.

I don't think we've spoken to one another since we were 16, but I still think about her every so often, and the dept of gratitude I owe her for her determination that I learn how to get her off. (And also for helping me learn to accept the fact that, through no fault of her or my own, it sometimes just wasn't going to happen.)

dear ms. 16,
wow is it easy to get caught up in your "disgust" with being a 16 year-old virgin. jesus christ. but seriously, i waited till i was almost 20, in a committed relationship, and knew how to give myself orgasms before i had sex for the first time. as soon as p was in v, i was like, "this is what all the fuss is about?!" the whole virginity thing was blown so out of proportion in my mind i wasn't able to get lost in the fun of sex even though i'd done everything "right" :(

most commenters here seem concerned your first time be as great as possible. in an ideal world, the dude you'd do it with would be awesome and you two could take time to learn how your bodies work together with minimal self-consciousness, and it would feel amazing ("hey, let's try to find my g-spot!"). but maybe you feel like you need to get it over with. if that's b/c of peer pressure, A Dude is totally right and you have shitty friends [who are probably having terrible sex...with losers].

so let's be rational. if you had the where-with-all to have this epiphany while getting fingered, your brain and body are probably not so overwhelmed with lust for this guy that sex is gonna be any better than getting a cucumber or a dildo crammed up there. if that doesn't sound like something that's gonna make you cum, just know that that's about what it's gonna feel like. only about 20% of women orgasm from vaginal penetration. why bother w/ this guy?

as others advise, wait for someone that's gonna be worth the effort. not b/c you'll be "in love" (tho you might be), but b/c at the very least it'll be more interesting and more fun.

Have 90% of you forgotten what it was to be 16 and horny, or even 16 and under lots of pressure from all different sides? It's not like this girl is 12, for chrissakes.

Anyway, here is what my advice would be:
First, learn about yourself. Learn how to get yourself off, what you like and what you don't, and make sure you understand how your body works (the number of women in their 20's I've had to explain the menstrual cycle to....). The internet can be helpful here.

Second, get contraception. Figure out how to get yourself on the pill, or get condoms. Yes, you get yourself some condoms, even though you're a girl. Do NOT have unprotected sex, no matter what.

Thirdly, figure out why you want to have sex. If the conclusion you come to has more to do with other people (my friends are all fucking like rabbits, i feel left out) vs yourself (i really want to know what that feels like) you may want to reconsider.

Finally, figure some more things out with this guy - or any guy. I really think the most important thing in a relationship is expectations - make sure you want the same thing from each other, and that you're on the same page. Which, based on the "ignoring him at school" line, doesn't sound like you guys are super-functional at the moment. If you're able to have a frank conversation about being friends-with-benefits, or at least define the relationship in some way, you'd be on better ground. Great sex can be all about love or it can have absolutely nothing to do with love - that's up to you and your partner. Emotions don't make sex magically more awesome, no matter what other commenters may say.

And if you do decide to go for it - the number of "oh, that was it?" virginity-loss stories I've heard from my friends vastly outnumber the "Rainbows and Unicorns and I am now an Enlightened Being" stories of first-time fucking.

I'm not saying fuck him, or don't fuck him - I'm just suggesting you think a lot of things over.

Maybe the 24 year old should just tell the immature prick that's trying to put things inside of her holiest of holies that it's her vaj and if he doesn't respect it or her enough to get tested than clearly he's still got a lot of growing up to do, and since she's not his mother he should fuck off, posthaste.

Seriously, twice you had to tell him? And his response was that? Are you sure he's of a consenting age in your state?

I don't think the 16-year-old was asking whether she should have sex with the "person of opposite gender." I think the bit to zero in on is, "in the midst of his heavy breathing and inept poking, I had an amazing epiphany: I had no idea if I was actually enjoying myself."

Girl, you will know if you're enjoying yourself. It sounds like you are slightly disgusted by this fellow, which is normal. Sexual behavior is kind of new to you and there's a thin line between hot/sexy and awkward/gross. By the way, this line continues into adulthood. The line is in different places for different people. (i.e. some girls are turned on by other girls, some girls find that makes them feel icky. Some people like role-play, some think it feels contrived and unsexy. Some people want to be watched, some don't. Some girls like hairless guys, some don't. Etc, etc. It's all good.)

Getting fingered at 16 is WAY different from sex. My vagina hurts just thinking about the "inept poking" in my own past. At first, guys finger the way they want their penis to be in you - fast and in and out - and that is really not what feels good to most ladies, and if you aren't excited (i.e. wet) it may even hurt. Plus they totally ignore, or mishandle, your clitoris, which is really where the energy should be here. Once a lady teaches them otherwise, they begin to change behavior.

My advice is to behave like a boy. No, I don't mean you should spray Axe on your nether regions and stuff tater tots in your mouth, I mean you should:

1. Dedicate some time to touching yourself, and know that it's your right and one of the great pleasures of humanity, whether or not you are sexually active. Don't worry about "doing it right," or even about getting to orgasm for awhile. Try slowly, circles, make sure everything is wet (spit will do here). Take your time and see what you find out.
2. Find some porn magazines. Not videos, magazines. Still photos, dirty stories. I stumbled on my dad's (ew, I know) Penthouse when I was a kid and the part that really got me going was Forum - the stories and scenarios. In fact, you have better options now, which leads me to...
3. Buy Bust magazine and flip to the back. There's a one-handed-read section (porn for ladies) and about a jillion ads for vibrators, underwear, etc. You might find a sex shop near you. If not, you might find that you can order from one (like Good Vibrations) in a discreet way w/o a credit card.
4. Remember that you have a lot of years and a lot of sexual experiences ahead of you - IF you use birth control EVERY TIME you don't want to have a kid. To prevent both disease and pregnancy, condoms are your best bet right now, with plenty of lubrication (not spermicidal, but more the Astroglide variety). And my health teacher was right, I think; if you're not ready to go buy these at the drug store (in the next town over), you're not ready for sex. It's good to develop the condom habit early, even if your guy hasn't been with anyone else, because later, you will probably be with someone who ISN'T a virgin, and you should use condoms until you've both been tested.

for some reason I can't actually edit, so I'll add:
1. I'm 32 and STILL finding new things that feel good, with and without my boyfriend, so you're in for a lifetime of really fun learning. Yay, learning!
2. I wish that those "survival packs" from health class told you how to begin masturbating as well as how to test for breast lumps.
3. A battery-operated electric toothbrush, the handle end, is a decent vibrator – don't put it directly on your clit until you know what you can handle, but that's a cheap option from your local drugstore and no one will suspect that you're doing anything but cleaning your teeth! plus the bristles may be interesting on your nipples. Find one with a rounded handle, not one that stands up on its own. Like this one...
http://www.amazon.com/CrossAction-Crossaction-Anti-Microbial-Battery-Toothbrush/dp/B00240XRUY/ref=pd_sim_hpc_1

I had pretty fantastic sex when I was 16 and 17, because I was a virgin, and extremely intent on not getting pregnant, so I fooled around with boys in every non-intercourse way I could think of which made things hot and creative. Here are the main two things I would say to a 16 yo today,
1. intercourse is over-rated! and risky! explore other things. For a long time I was a big fan of dry humping and totally would come that way. Often, so would the dude! I had oral sex for the first time when I was 17. It wasn't THE BEST THING EVER at first, but I noticed that if the dude and I spent a loooooooong time making out and rubbing up on each other and basically getting super worked up, by the time the underwear came off, orgasm was imminent.

2. I think masturbating is key. Don't give up. The better lover you are to yourself, the better sex you will have with a partner. There is a great teen sex website called scarleteen that actually has a how to masturbate article. The other thing about masturbating is that it really has to be inspired at first. If you are trying to jerk off because you are frustrated and all "god damn it, I WILL learn to do it right," then you are stacking the deck against yourself. Your brain has to be harder/wetter than your clit for masturbating to be easy and as fun you need to stay motivated, imo. If I were you I would look for erotica, nude photos of someone (like a movie star or something) that turns you on, or love scenes in movies that turn you on and try and go from there. I would avoid outright porn at first because, it can also have a totally OPPOSITE effect and make you never want to have sex or be naked ever again. (This effect, for the most part, is temporary.)

Sexuality is the most amazing and most confounding part of being a human being, as far as I am concerned. Luckily, you are going about getting what you want early on, you are not willing to go through pain and bullshit and that is awesome. I think that is more than half the battle. Be patient with yourself. If you have the guts to ask about this and really try and have a good sexual experience now, then I would be that you have a lot of awesome sex to look forward to. You'll get there. Enjoy the process on the way.

Adding my voice to the chorus of lady-people who had good sex in their teens. Of course, prior to doing it a lot with my high school boyfriend, I masturbated for about 8 years.

FUN TIPS:
DON'T WORRY ABOUT *WHEN* YOU LOSE IT, worry about who you lose it to. I'll definitely support the idea that early sexings are better if emotions are involved. If only because the guy, however inept, cares how you feel.

MASTURBATE SO MUCH. Get practice at coming in different ways (with hands, with vibe, with penetration, with clit stim, on your stomach, on your back, etc). Visit dodsonandross.com for pointers.

DON'T SELL YOURSELF SHORT. A Dude says that all teenage boys are, basically, bad lays. Also in college. Hold yourself (and your partner/s) to a higher standard! Bad sex is not inevitable! Don't be afraid to spend time seeking out what feels good for *you* when you're with somebody.